Things To Do
Chicago Architecture Boat Tour
One of the best ways to experience the city! We did the architecture tour on our 7th anniversary date, and it is amazing. For those of you who are more adventurous, you can also kayak along the Chicago River. It is a blast! Please note: Andy once built a raft and attempted to float down the river himself. He quickly found out this is strictly prohibited.
The 606 - Bloomingdale Trail
This abandoned rail line turned park connects the Wicker Park and Logan Square neighborhoods. In the early days, Andy would meet up with Kat on the trail while she was babysitting and taking the baby for a walk. During lockdown, this trail was a lifesaver. We've gone on countless dates walking the 606 to get ice cream. Take a walk and stop at some of our favorite spots for a sweet treat: Margie's Candies on Western or Small Cheval on either Milwaukee or Armitage. At Ava's Italian Ice, you might run into Chance the Rapper!
Chicago Transit Authority
If you know Andy, you know he has a particular affinity for public transportation. One of his favorite things about living in Chicago is "riding the choo choo." We call the Blue Line home and can vouch for its new 7000-series cars, but explore any of Chicago's "L" (short for "elevated") train lines, and you are bound to have an adventure! If you want to check out downtown, you can take a train headed for the Loop. Bonus points if you spot Sandy B!
The Up Room at the Robey Hotel
Walkable from our apartment, the historic Robey Hotel was one of the first skyscrapers to be built in Chicago outside of the downtown area. Take the elevator up to their awesome rooftop lounge. You can go for the delicious cocktails (Kat loves the Last Word) or just check out the beautiful view of the Chicago Skyline!
Irazu Costa Rican Restaurant
This Costa Rican restaurant is one of Andy's all-time favorite lunch spots, right by his old Bucktown apartment. We love the Pepito Sandwich, a yummy family recipe served on French bread. And don't just take our word for it- Guy Fieri visited on DDD and loved it!
Lincoln Park Zoo
A wonderful way to spend the afternoon. We went on one of our very first "friend hangs" to go see ZooLights at Christmastime, and we try to make it a yearly tradition.
Garfield Park Conservatory
Considered revolutionary when it opened in 1908, the Garfield Park Conservatory is a great place to walk around. The Fern Room is stunning, and the conservatory's warmth comes in clutch for surviving Chicago winters.
Pequod's Pizza
If you haven't ever tried deep dish pizza, it's a must. Although Kat prefers her beloved NY-style slice, this Chicago tradition (more similar to a pot pie) shouldn't be skipped. There is of course Lou Malnati's and Giordano's, but Pequod's is our favorite. Warning: pizzas come out in appr. 45 minutes and are INCREDIBLY filling. Chicago also has great spots for NY- and Detroit-style pizzas. We frequent Piece Pizzeria for New Haven-style pizza, which we ordered the night we got engaged to celebrate with our friends. Try their white clam pizza or Kat's fav: the Honey Butter Fried Chicken (HFBC) pie.